Isolation of a new flavonoid from Prasium majus L. with evaluation of its potential biological activities.

In line with the importance of Prasium majus L. (Lamiaciatae) in traditional medicine as a calming and sedative remedy, the present study was designed to reveal its chemical constituents and bioactivity potentials. Thus, after extraction and fractionation of the plant material, the obtained butanol fraction (BPm) was subjected to conventional chromatographic separation of its constituents in addition to LC-MS/MS evaluation versus some authentic standards. The study resulted in the isolation and characterisation of 8 compounds, including one new chrysoeriol derivative, majusiode (1). Structural elucidation of all isolated compounds was based on detailed investigation of their spectral data (NMR (1 & 2D), ESI-MS, IR and UV-Vis). HPLC-MS/MS analysis versus authentic samples lead to the detection of 31 constituents, including all 8 isolated compounds. The new compound (1) showed moderate AChE inhibition power (IC50: 163.3 ± 3.4 µg/mL) as compared to the positive control galanthamine (91.4 ± 5.2 µg/mL) and moderate DPPH•/ABTS•+ scavenging power.

Uncovering the Chemical Composition and Biological Potentials of Bupleurum lancifolium Hornem. from Jordan.

The current study was designed to uncover the chemistry and bioactivity potentials of Bupleurum lancifolium growing wild in Jordan. In this context, the fresh aerial parts obtained from the plant material were subjected to hydrodistillation followed by GC/MS analysis. The main components of the HDEO were γ-patchoulene (23.79%), ß-dihydro agarofuran (23.50%), α-guaiene (14.11%), and valencene (13.28%). Moreover, the crude thanolic extract was partitioned to afford two main major fractions, the aqueous methanol (BLM) and butanol (BLB). Phytochemical investigation of both fractions, using conventional chromatographic techniques followed by careful inspection of the spectral data for the isolated compounds (NMR, IR, and UV-Vis), resulted in the characterization of five known compounds, including α-spinasteryl (M1), ethyl arachidate (M2), ethyl myristate (M3), quercetin-3-O-ß-d-glucopyranosyl-(1-4")-α-L-rhamnopyranosyl (B1), and isorhamnetin-3-O-ß-d-glucopyranosyl-(1-4")-α-L-rhamnopyranosyl (B2). The TPC, TFC, and antioxidant activity testing of both fractions and HDEO revealed an interesting ABTS scavenging potential of the BLB fraction compared to the employed positive controls, which is in total agreement with its high TP and TF contents. Cytotoxic evaluation tests revealed that BLM had interesting cytotoxic effects on the normal breast cell line MDA-MB-231 (ATCC-HTB-26) and the normal dermal fibroblast (ATCC® PCS-201-012) and normal African green monkey kidney Vero (ATCC-CCL-81) cell lines. Despite both the BLB and BLM fractions showing interesting AChE inhibition activities (IC50 = 217.9 ± 5.3 µg/mL and 139.1 ± 5.6 µg/mL, respectively), the HDEO revealed an interestingly high AChE inhibition power (43.8 ± 2.7 µg/mL) that far exceeds the one observed for galanthamine (91.4 ± 5.2 µg/mL). The HDEO, BLM, and BLB exhbitied no interesting antimicrobial activity against Bacillus cereus, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, or Pseudomonas aeruginosa.

Unveiling the Impact of Drying Methods on Phytochemical Composition and Antioxidant Activity of Anthemis palestina.

Different drying techniques may alter the chemical composition of plant extracts and consequently affect their bioactivity potential. The current study was designed to reveal the effect of four different drying methods on the phytochemical composition and antioxidant activity of hydrodistilled essential oil (HD-EO) and methanolic (APM) extract obtained from the aerial part of Anthemis palestina from Jordan. Aerial parts of A. palestina in their fresh (FR) form and after drying in shade (ShD), sun (SD), oven at 40 °C (O40D) and 60 °C (O60D), in addition to microwave (MWD), were used to extract their essential oils by hydrodistillation and to prepare the different methanolic extracts (APM). GC/MS analysis of the different HD-EOs revealed qualitative and quantitative differences among the different samples. While FR, O40D, O60D, and MWD EO samples contained mainly sesquiterpene hydrocarbons (35.43%, 29.04%, 53.69%, and 59.38%, respectively), ShD sample was rich in oxygenated monoterpenes (33.57%), and SD-EO contained mainly oxygenated sesquiterpenes (40.36%). Principal component analysis (PCA) and Cluster analysis (CA) grouped the different drying methods based on their impact on the concentration of chemical constituents. SD-EO demonstrated high DPPH and ABTS antioxidant activity (1.31 ± 0.03) × 10-2; (1.66 ± 0.06) × 10-2 µg/mL, respectively). Furthermore, A. paleistina methanolic extracts (APM) obtained after subjecting the plant to different drying methods showed interesting patterns in terms of their TPC, TFC, antioxidant activity, and phytochemical profiling. Of all extracts, SD-APM extract had the highest TPC (105.37 ± 0.19 mg GA/g DE), highest TFC (305.16 ± 3.93 mg Q/g DE) and demonstrated the highest DPPH and ABTS scavenging activities ((4.42 ± 0.02) × 10-2; (3.87 ± 0.02) × 10-2 mg/mL, respectively); all were supported by correlation studies. LC-MS/MS analysis of the different extracts revealed the richness of the SD-APM extract in phenolic acids and flavonoids.

Scrophularia peyronii Post. from Jordan: Chemical Composition of Essential Oil and Phytochemical Profiling of Crude Extracts and Their In Vitro Antioxidant Activity.

The genus Scrophularia is one of the largest genera belonging to the Scrophulariaceae family. Different members of the genus exhibit an interesting, wide spectrum of bioactivities. Accordingly, the current study aimed to investigate, for the first time, the chemical composition of the essential oil of Scrophularia peyronii Post. from Jordan. Additionally, extracts obtained from the aerial parts with solvents of different polarities were assayed for their phytochemical constituents and in vitro antioxidant activities. The major constituents detected in the essential oil, as revealed by GC/MS analysis, contained mainly Z,Z-farnesyl acetone (11.04%), ß-elemene (6.36%), n-octanal (5.98%), and spathulenol (4.58%). Each of the aqueous methanol (Sp-M) and butanol (Sp-B) extracts contained flavonoids, saponins, anthraquinone, and glycosides. Both extracts were evaluated for their total phenolic content (TPC), total flavonoid content (TFC), and their in vitro antioxidant activity, which were assayed using the DPPH radical scavenging activity and ABTS radical scavenging methods. Additionally, the two extracts were then subjected to LC-ESI-MS/MS for the qualitative determination of their secondary metabolite content, especially in flavonoids and phenolic compounds. The results showed that the Sp-B extract of S. peyronii had the highest contents of both phenolic compounds and flavonoids and showed high radical scavenging activity, as determined by the two assay methods, when compared with the Sp-M extract. The LC-ESI-MS/MS analysis resulted in the detection of 21 compounds, including 8 flavonoids, 6 phenolic acids, 6 iridoids, and 2 acids. Although the majority of compounds were detected in both extracts, it was noticed that scropolioside B, 6'-O-cinnamoylharpagide, isoferulic acid, and 6-O-methylcatapol were only detected in the Sp-M fraction.

LC-MS/MS Screening, Total Phenolic, Flavonoid and Antioxidant Contents of Crude Extracts from Three Asclepiadaceae Species Growing in Jordan.

This study aimed to evaluate the antioxidant activity and total phenolic content (TPC) and total flavonoid content (TFC) of crude extracts obtained from three Asclepiadaceae species, namely, Calotropis procera L., Peruglaria tomentosa L., and Pentatropis spiralis (Forsk.) Decne. Both butanol and aq. methanol extracts of the three species showed the highest amount of phenol and flavonoid contents, which exhibited the greatest antioxidant activity in the scavenging of 2,2-diphenyl-2-picrylhydrazyl free radical (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt radical cation (ABTS), ferrous chelating effect (FIC), and hydroxyl radical (HDR) assays. Phytochemical screening of the extracts revealed the presence of alkaloids, tannins, sponins, flavonoids, terpenoids, and glycosides. LC-MS analysis was carried out to identify the major compounds from each crude extract. A total of 12 phenolic compounds in the extracts of the 3 species were identified and quantified, including 9 flavonoids, 2 hydroxybenzoic acids, and 3 hydroxycinnamic acids. The current study also revealed a good correlation between total phenolic contents and the observed antioxidant activity of the crude extracts.

Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 2-Azides, Phthalocyanines, Subphthalocyanines and Porphyrazines.

The reaction between organic azides and alkyne derivatives via the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) is an efficient strategy to combine phthalocyanines and analogues with different materials. As examples of such materials, it can be considered the following ones: graphene oxide, carbon nanotubes, silica nanoparticles, gold nanoparticles, and quantum dots. This approach is also being relevant to conjugate phthalocyanines with carbohydrates and to obtain new sophisticated molecules; in such way, new systems with significant potential applications become available. This review highlights recent developments on the synthesis of phthalocyanine, subphthalocyanine, and porphyrazine derivatives where CuAAC reactions are the key synthetic step.

Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1-Azides, Porphyrins and Corroles.

Azides and porphyrinoids (such as porphyrin and corrole macrocycles) can give rise to new derivatives with significant biological properties and as new materials' components. Significant synthetic approaches have been studied. A wide range of products (e.g., microporous organic networks, rotaxane and dendritic motifs, dendrimers as liquid crystals, as blood substitutes for transfusions and many others) can now be available and used for several medicinal and industrial purposes.

Chemical constituents of the aerial parts of Salvia judaica Boiss. from Jordan.

Investigation of the chemical constituents of Salvia judaica growing wild in Jordan led to the isolation and identification of 15 known compounds. These included: luteolin-3'-methyl ether (1), indole-3-carboxyaldehyde (2), p-hydroxybenzaldehyde (3), tricin (4), apigenin (5), methyl isoferuloyl-7-(3,4-dihydroxyphenyl) lactate (6), methyl rosmarinate (7), rosmarinic acid (8), salvigenin (9), ß-sitosterol (10), 3ß, 28-dihydroxyurs-12-ene (11), cirsilineol (12), 2,3-dihydroxyurs-12-en-28-oic acid (13), ß-sitosteryl glucoside (14), and tormentic acid (15). Compounds 6 and 7 exhibited strong radical scavenging and chelating activities as compared to α-tocopherol and ascorbic acid, compound 7 showed a 2-fold greater antioxidant activity as compared to compound 6. Furthermore, low doses of compounds 6 and 7 were able to inhibit the growth of leukemic (HL-60, Jurkat, K562 and CCRF-SB) and solid tumor cells (MCF-7, MDA-MB-231 and Caco-2). Compound 7 showed a ca. 3-4-fold stronger cytotoxicity against the tested cells as compared to compound 6.

Evaluation of Triazole and Isoxazole Derivatives as Potential Anti-infective Agents.

A series of isoxazole and triazole derivatives, with interesting bioactive scaffolds, were examined for their in vitro antibacterial, antifungal, and antiprotozoal activities. These compounds exhibited antitrypanosomal activity comparable to difluoromethylornithine (DMFO), a drug used in the treatment of human African trypanosomiasis. Isoxazole analogues 1, 3 and 4, and triazole derivatives 16, 17, 28, 37, 40 and 42 showed the highest antitrypanosomal activity with IC50 values of 17.89, 1.82, 10.38, 10.26, 11.77, 9.29, 3.93, 2.11, and 0.93 µM, respectively. Compounds 40 and 42 showed the most potent activity against Leishmania donovani amastigotes with IC50 values of 18.28 and 10.54 µM, respectively. Compound 42 showed the most potent activity against Leishmania donovani macrophage internalized amastigotes with an IC50 value of 8.32 µM. Conjugate triazoles 40-43 displayed potential antimalarial activity against chloroquine-resistant W2 and chloroquine sensitive D6 Plasmodium falciparum strains (IC50 value range from 0.58 to 8.36 µM). Compound 37 showed antibacterial activity against Staphylococcus aureus, MRSA and Mycobacterium intracellulare with IC50 values of 15.53, 14.22 and 47.45 µM, respectively. None of the compounds exhibited antifungal activity.

New flavonol glycoside from Scabiosa prolifera L. aerial parts with in vitro antioxidant and cytotoxic activities.

Phytochemical investigation of the chemical constituents of the aerial parts of Scabiosa prolifera L. led to the isolation of one new flavonol glycoside, kaempferol-3-O-(4″,6″-di-E-p-coumaroyl)-ß-D-galactopyranoside (1), along with ten other known compounds including luteolin-7-O-(2″-O-ethyl-ß-glucopyranoside), ß-sitosterol, ß-sitosterylglucoside, ursolic acid, corosolic acid, ursolic acid 3-O-ß-D-arabinopyranoside, apigenin, methyl-α-D-glucopyranoside, luteolin-7-O-ß-glucopyranoside and isoorientin. The structures of all isolated compounds were established using chemical methods and spectroscopic methods including IR, UV, NMR (1D and 2D) and HRESIMS. All compounds were isolated for the first time from the plant. The antioxidant and cytotoxic activities of compounds 1 and 2 were also investigated.

New isoflavones from Gynandriris sisyrinchium and their antioxidant and cytotoxic activities.

Chemical investigation of Gynandriris sisyrinchium (L.) Parl growing in Jordan resulted in the isolation and characterization of a total of twelve compounds two of which are reported here for the first time in nature. These new compounds included the isoflavones; 3'-methyl tenuifone (2) and gynandrinone (5). In addition, ten known compounds including; ß-sitosterol (1), 7,3'-dimethoxy-5,6,4'-trihydroxyisoflavone (3), iristectorigenin (4), hispidulin (6), galangustin (7), 6-hydroxybiochanin A (8), ursolic acid (9), ladanetin (10), 4'-O-methylgenistein (11) and ß-sitosterol glucoside (12) are also reported here for the first time from G. sisyrinchium. The isolated compounds were characterized by different spectroscopic methods including NMR (1D and 2D), UV, IR and MS (HRESIMS and EIMS). The antioxidant and cytotoxic activities of isoflavones 2, 3 and 5 were investigated. Compound 3 showed the highest antioxidant activity (IC50=17.3µg/mL), as compared to compounds 5 and 2 (IC50=26.7 and 51.7µg/mL, respectively). The cytotoxic activity against the human promyelocytic leukemia HL-60 cells revealed that compound 2 was the most active (40µM). The results indicate that the cytotoxicity of compound 2 is mediated by apoptosis.

Flavonoid and phenolic compounds from Salvia palaestina L. growing wild in Jordan and their antioxidant activities.

Investigation of the butanol fraction of Salvia palaestina Benth. from Jordanian origin resulted in the isolation and characterization of nine compounds, three of which are reported here for the first time in Nature. These compounds included the two phenolics: salpalaestinin (1), methyl 3-O-methylrosmarinate (3) and the flavonoid luteolin 7-O-(2″-p-hydroxybenzoyl)-ß-glucuronide) (8). In addition, 3,4-dihydroxyphenyl caffeate (2), diosmetin (4), apigenin-7-O-(6″-butyryl-ß-glucopyranoside) (5), luteolin-3'-O-methyl-7-O-(6″-butyryl-ß-glucopyranoside) (6) and clinopodic acid B (7) were also obtained from the butanol fraction of the plant. The structures of the isolated compounds were elucidated by different spectroscopic methods including NMR (1D and 2D), UV, IR and MS (HRESIMS and EIMS). The DPPH radical scavenging activity for compounds 1, 3, 5, 6 &8 was evaluated. Compound 3 had the highest antioxidant activity (91.9±1.30% inhibition) with an IC50 value of 1.0±0.23(µg/mL).